Water → HCID 57925844, compound

HRID 1013530Notes

Reaction equation

HRID 1013530 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:11][C:12]2[CH:13]=[C:14]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:15]=[CH:16][C:17]=2[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:10])=[CH:5][CH:4]=1.[C:32]1(=[O:42])[NH:36][C:35](=[O:37])[C:34]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:33]12.[K].[I-].[K+].O>CN(C=O)C>[O:37]=[C:35]1[C:34]2[C:33](=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:32](=[O:42])[N:36]1[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:11][C:12]2[CH:13]=[C:14]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:15]=[CH:16][C:17]=2[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:10])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 24194345Phthalimide potassium saltHCID 57925998N-[3-[[4-(Chloromethyl)benzoyl]amino][1,1'-biphenyl]-4-yl]carbamic Acid tert-Butyl Ester

Product 1

HCID 57925844HCID 57925844, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,1-dimethylethyl [3-({[4-(chloromethyl)phenyl]carbonyl}amino)biphenyl-4-yl]carbamate (20 g, 45.8 mmol), potassium phthalimide (9.33 g, 50.4 mmol) and potassium iodide (1.52 g, 9.15 mmol) were stirred in DMF (81 mL) at 50° C. overnight. Room temperature was attained, H2O was added and the products extracted into EtOAc (×2). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was triturated in MeOH to give 1,1-dimethylethyl {3-[({4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}carbonyl)amino]biphenyl-4-yl}carbamate as a pale yellow solid.

Workup

  1. customRoom temperature
  2. extractionthe products extracted into EtOAc (×2)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated in MeOH

Sources & evidence

ORD record
ord-307300db7d7c481c9ad9a39d081ce7da
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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